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Gary Dressel has a diverse work experience spanning over two decades. Gary began their career in 1998 as a Route Sales Driver at The Schwan Food Company. From 1999 to 2005, they worked in Human Resources at Teleplan Wireless. In 2005, Gary joined Hutchinson Technology Inc., where they took on roles as a Technical Recruiter and later as a Technical Recruiter/HR Generalist. Gary then moved on to Motorists Commercial Mutual Insurance Company in 2008 and held multiple positions including Human Resource Specialist, Corporate Services Manager, and Director of Operations. In 2017, they joined Motorists Insurance Group as HRIS Director. Currently, Gary is the Director of HRIS & Payroll at Encova Insurance.

Gary Dressel attended Southwest Minnesota State University from 1994 to 1998, but did not complete a degree or declare a field of study.